The contacting of a plant oil, carboxylic acid and hydrogen peroxide is well documented and can easily be found in the public domain. The focus of prior work in this area has been the preparation of epoxides and polyols from unsaturated triglycerides found commonly in a wide range of oil seeds.
These epoxides and polyols are polymerized with isocyanates to form polyurethanes, the isocyanate reacting with active epoxide and hydroxyl sites. The manufacture of these products using the materials outlined above requires heat, agitation, and owing to solubility limitations of the components, involves more than one liquid phase.
The desired end product of the resulting polyol is one that has active primary and secondary hydroxyl sites, with no interfering or competing functional groups. The desired end product of the resulting epoxide is a product that has no active, interfering or competing primary or secondary hydroxy sites. There has been very little work done on the preparation and use of hybrids comprised of active epoxide and hydroxyl sites in the same molecule and end use applications of the same.
This technology extends to the use of all mono and poly-unsaturated plant and animal derived triglycerides including those that have undergone transesterification to form esters, in what is commonly known as the biodiesel process.
Camelina sativa is a cruciferous oilseed plant. Also known as false flax or gold of pleasure, this natural oil source has been in use since Bronze and Iron Ages. The seeds contain 30-40% oil on a dry basis. The oil finds use in cooking and high omega-3 preparations such as salad dressing, mayonnaise, ice cream, pet foods, and, biodiesel. It has a fatty acid profile of 10% of saturated, 34% mono-unsaturated and 56% poly-unsaturated, with alpha-linolenic acid accounting for 35% of the oil.
The unsaturated fatty acid sites in camelina oil and all triglycerides are composed of carbon-carbon double bonds. These alkene sites are of particular interest in the preparation of functionalized plant oils for industrial use. This oil fits very well into the instant invention, in that, the oils that are preferred are those oils, or combination of oils that have up to C22 carbon atoms.
These reactive alkene sites offer an opportunity to transform the camelina and other plant or animal derived oils into value added products suitable for use in the polyurethane, healthcare, energy, and other industries.
This invention is directed to a process for transforming these oils into reactive intermediates that contain moieties with a combination of alkenes, and either hydroxyl or epoxide, or a combination of hydroxyl and epoxide, reactive sites in the same product.